As the dust settled on the evacuation of Afghanistan in 2021, the Kabul airlift brought an inauspicious end to America’s twenty-year adventure in the Graveyard of Empires. Over two tumultuous weeks in August, some 28,000 people were evacuated to safety in an effort reminiscent to many of the 1975 fall of Saigon.
What began in the weeks after the 9/11 attacks culminated with the fall of Kabul and President Ashraf Ghani fleeing his palace to the safety of Tajikistan. America’s longest war had ended ingloriously, the kind of hollow conclusion that haunted the military in the decades after the end of the Vietnam War. Much like that earlier conflict, the war in Afghanistan was marked with overwhelming tactical success, but strategic failure. Through multiple administrations and a revolving door of senior military leaders, no one had been able to connect victory at the tactical level to any modicum of strategic success.
That disconnect was not without precedent, something Sun Tzu warned of The Art of War: “Tactics without strategy is the noise before defeat.”
The Astrategic Approach
“But we had a strategy,” is a response I’ve heard more times than I can count. It’s true. We did have a strategy. Several of them, in fact. But a bad strategy—or one uniformed by reality—is as good as not having a strategy.
When we first entered Afghanistan in September 2001, we were understandably angry and looking for a fight. But, beyond eradicating al Qaeda, defeating the Taliban, and capturing Osama bin Laden, we didn’t have any immediate long-term objectives. We were committing another error that Sun Tzu cautioned against: “He who is destined for defeat fights first and afterwards looks for victory.” But we were hardly the first to make that mistake.
The astrategic approach is much more common than most people realize. The typical strategic plan—which is sort of an oxymoron in and of itself—employed by organizations under the guise of actual strategy is often little more than a collection of initiatives that may or may not be aligned with a strategic vision or have resources allocated against them. These plans aren’t truly all that strategic, just elaborate to-do lists that look impressive when presented as oversized poster boards and brief well to PowerPoint weary audiences. They’re Easy Button solutions to complex problems.
Strategy is hard. It takes time. It demands discipline and focus. It’s not a pick-up game. Forget the checkers and chess analogies; strategy is a Rubik’s sphere with infinite possible outcomes driven by an incalculable number of variables. Getting it right requires years of study and practice, and countless hours reflecting on theory that is often so deeply metaphorical you might as well be reading the Old Testament.
10 Strategy Reads for the New Year
Finding good books that deal with strategy or strategy-related topics isn’t that difficult. Narrowing that list to what matters most is never easy, and the end result is always debatable. Regardless of what I might recommend for someone to read, someone else will always have a different perspective. I respect that, honestly, because learning is a journey of discovery, and we should always be open to new ideas when it comes to subjects that are important to us.
When it comes to strategy, the aim should be to build a body of knowledge that evolves gradually with our learning. Every book brings new ideas, and our understanding and mastery of the strategic art grows with time.
The Classics:
- On War, by Carl von Clausewitz. Oft quoted, rarely read, but absolutely fundamental to understanding strategy. Context is critical when reading Clausewitz; you have to understand the period in which he was writing and the events of the time, coming in the aftermath of the Napoleonic wars.
- The Art of War, by Sun Tzu. A timeless classic that sets the roots of our principles of war, which apply broadly to any form of competitive strategy. The Art of War is a remarkably short read that packs a powerful punch. Take time to reflect on every book.
- The Book of Five Rings, by Miyamoto Musashi. On the surface, The Book of Five Rings is about Japanese swordsmanship and the martial arts broadly. But Musashi’s metaphorical writing addresses conflict and strategy in a deeply philosophical sense. Like Sun Tzu, this is writing that requires a fair amount of reflection to appreciate.
- The Prince, by Niccolò Machiavelli sometimes gets a bad rap. The Prince is one of the first works of modern political philosophy, and as Clausewitz reminds us, strategy and politics are inseparable.
The Basics:
- On Grand Strategy, by John Lewis Gaddis. In a world where everyone wants to wax proudly about their strategic plans, grand strategy is the red-headed stepchild in the room. The longer you ignore it, the worse your problems get. Gaddis is here to remind you that grand strategy still matters.
- On Competition, by Michael Porter. In the world of business strategy, Porter is The Godfather. He understands one fundamental truth about strategy that others often neglect: strategy is competitive by nature, a brutal knife fight that ends when your rivals no longer possess the will to continue.
- Thinking Fast and Slow, by Daniel Kahneman. The foundation of effective—and successful—strategy is decision making. As a result, understanding how and why you make the decisions you do, how your mind works, is the secret sauce of strategy.
The Finer Points:
- ReCulturing, by Melissa Daimler. Peter Drucker’s observation that “culture truly eats strategy for breakfast” is a fundamental truth. Yet most strategic efforts ignore organizational culture. Daimler is here to help you help yourself.
- Moneyball, by Michael Lewis. “Data literate” is one of the most exhausted buzzwords in use today. People who made an effort to understand data always had an edge over those who didn’t; Moneyball’s central premise is that the data literacy is a moving target and if you’re not paying close attention, you’re going to get left behind.
- Measure What Matters, by John Doerr. Assessment is one of the least sexy—but most important—elements of strategy. You are far less likely to achieve your objectives if you can’t measure progress toward them. Doerr’s system is simple and painless, and it works.
To be fair, it’s impossible to narrow any list of necessary strategy books to just ten titles. It’s far easier to name books that aren’t useful than to select just a few that are. Inevitably, there are books that don’t make this list that should be here, and one of those is William Duggan’s Strategic Intuition. Unlike the rapid thinking exemplified by expert intuition in Malcolm Gladwell’s 2005 book, Blink, Duggan explores how intuition works in unfamiliar situations where the mind requires more time to recognize patterns and make the mental connections required for strategic decision making.
